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Anti-Inflammatory Effects of Flavonoids in Citrus Jabara Fruit Peels

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Anti-Inflammatory Effects of Flavonoids in Citrus Jabara Fruit Peels Trends in Immunotherapy (2020) Volume 4 Issue 1. doi: 10.24294/ti.v4.i1.844 Original Article Anti-inflammatory effects of flavonoids in Citrus jabara fruit peels Seisho Azuma1,2§, Yoshinobu Murakami1§*, Eiko Azuma2, Kimiye Baba1, Masahiko Taniguchi1 1 Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan 2 Jabara Laboratory, 4-7-18 Matsue Kita, Wakayama 640-8425, Japan §: Both authors contributed equally to this work. ABSTRACT Currently, about half of people in Japan suffer from allergic diseases. Thus, Citrus jabara fruits have been paid attention as one of quite effective anti-allergic functional foods. C. jabara is an endemic species originally grown only in Kitayama village, Wakayama prefecture in Japan. Although genetic characterization and diversity of various Citrus fruits including C. jabara were researched, but there is room for the study on flavonoids characteristics in C. jabara fruit. For the alleviation of allergic symptom, anti-inflammatory effects are also important. In this study, characteristics of flavonoids in C. jabara fruit peels, and the anti-inflammatory effects of these purified flavonoids were investigated. Our results revealed that C. jabara is a unique Citrus that almost all of flavonoids in fruit peels was narirutin. There was no Citrus species with a flavanone glycosides content ratio like C. jabara. Although anti-inflammatory effects of narirutin was weak, but its aglycone naringenin exhibited following inhibitory effects: nitric oxide synthesis (IC50 = 105 μM), nitric oxide synthase induction, Interleukin-6 synthesis (IC50 = 65 μM), and inducible soluble epoxide hydrolase activity (IC50 = 267 μM). Since narirutin is deglycosylated to naringenin that is then absorbed by colonocytes, it is considered that narirutin exists like a prodrug and its aglycone naringenin works as an active form of anti-inflammatory effect in a living body at oral ingestion of C. jabara fruit peels. Keywords: Citrus jabara; anti-inflammatory effects; flavonoids; narirutin; naringenin ARTICLE INFO Received: March 6, 2020 Introduction Accepted: April 1, 2020 Available online: April 15, 2020 Currently, about half of people in Japan suffer from allergic diseases such as pollen allergy, perennial rhinitis, and atopic dermatitis. So, it is figuratively *CORRESPONDING AUTHOR said that allergic diseases are the current national disease in Japan. Under such Yoshinobu Murakami, 4-20-1 condition, the functional foods to alleviate allergic symptoms, such as Citrus Nasahara, Takatsuki, Osaka 569-1094, [1,2] Japan; [email protected] unshiu unripe fruit, were focused . CITATION In recent years, Citrus jabara fruits has also been paid attention as one of Azuma S, Murakami Y, Azuma E, et quite effective anti-allergic functional foods. C. jabara is an endemic species al. Anti-inflammatory effects of flavonoids in Citrus jabara fruit peels. originally grown only in Kitayama village, Wakayama prefecture in Japan, Trends Immunother 2020; 4(1): 5-14. and is estimated as a natural hybrid species of Citrus junos, Citrus reticulata, doi: 10.24294/ti.v4.i1.844 and Citrus kinokuni[3]. C. jabara was recognized as a new variety of citrus by Dr. Tanaka in 1971, and then registered as a new nursery plant in 1979 by Mr. COPyRIGHT Copyright © 2020 by author(s) and Fukuda (Japan the plant variety protection NO. 10). Concerning with anti- EnPress Publisher LLC. This work is allergic activities of C. jabara fruits, the anti-degranulation activity[3], the licensed under the Creative Commons improving effect of its juice on symptoms and quality of life in patients with Attribution-NonCommercial 4.0 [4] International License (CC BY-NC 4.0). Japanese cedar pollinosis , and the suppressive effect of its extracts on mucin http://creativecommons.org/licenses/ production in human lung epithelial cells[5] were reported. Although genetic by/4.0/ characterization and diversity of various citrus fruits including C. jabara were researched [6–8], but there is room for the study on flavonoids characteristics in C. jabara fruit. For the alleviation of allergic symptom, both anti-allergic effect and anti-inflammatory effects are important. Thus, in this study, we investigated the component analysis of flavonoids in C. jabara fruit peels and the anti-inflammatory effects of these isolated flavonoids. 5 Anti-inflammatory effects of flavonoids in Citrus jabara fruit peels Materials and Methods (FLV6, 2.9 mg), retusin (5-hydroxy-3, 3’, 4’, 7-tetramethoxyflavone) (FLV7, 1.9 mg), Extract and isolation nobiletin (3’, 4’, 5, 6, 7, 8-hexamethoxyflavone) (FLV8, 1.9 mg), three flavanones: 3’, 4’, 5, 6, 7, C. jabara fruits were harvested in Kitayama 8-hexamethoxyflavanone (FNN2, 32.1 mg), 3’, village, Wakayama prefecture in Japan and on 3 4’, 5, 6, 7-pentamethoxyflavanone (FNN3, 6.7 November 2010. The residue of C. jabara fruits by mg), 4’, 5, 6, 7-tetramethoxyflavanone (FNN4, commercial roller juice squeezer was used as C. 1.4 mg), three chalcones: 2’-hydroxy-3, 3’, 4, 4’, jabara fruit peels. After drying, these peels were 5’, 6’-hexamethoxychalcone (CHL1, 31.7 mg), chopped and sealed in aluminum puck until use. 2’-hydroxy-3, 4, 4’, 5’, 6’-pentamethoxychalcone Extract and isolation were carried out in 2010. ( CHL2, 8.2 mg), 2’-hydroxy-4, 4’, 5’, 6’-tetramethoxychalcone (CHL3, 7.8 mg). The The dried of C. jabara fruit peels (1 Kg) EtOAc and acetone residues were filtered to obtain were chopped into small pieces and extracted an amorphous powder (narirutin: FNN1, 17.7 g). with n-hexane (3 L x 5), EtOAc (3 L x 3) and These compounds were determined by comparison acetone (3 L x 3) using a ultrasonic extraction. of physical data and NMR spectral data with The combined n-hexane, EtOAc and acetone [9–13] articles . extracts were concentrated to dryness in vacuo, respectively. The n-hexane residue (11.7 g) was Chemical structures of isolated compounds were subjected to column chromatography on silica shown in Figure 1, and their names and amounts gel and ODS, and eluted successively with a were listed in Table 1. Among these compounds, n-hexane – EtOAc and MeOH – H2O solvent FLV3, 5, 6, 7 and CHL1-3 are the compounds which system to afford fourteen compounds, eight were isolated for the first time from C. jabara fruit flavones: 3, 3’, 4’, 5, 6, 7, 8-heptamethoxyflavone peels[14]. Seven compounds that were obtained more (FLV1, 265.8 mg), natsudaidain (3-hydroxy-3’, than 10 mg (FLV1 - 4, FNN1 - 2, and CHL1) were 4’, 5, 6, 7, 8-hexamethoxyflavone) (FLV2, evaluated in cell-based assays. 130.3 mg), 5-hydroxy-3, 3’, 4’, 6, 7, 8-hexamethoxyflavone (FLV3, 29.3 mg), Materials 3, 3’, 4’, 5, 6, 7-hexamethoxyflavone (FLV4, 14.6 mg), 8-hydroxy-3, 4’, 5, 6, Naringenin was purchased from LKT Laboratory 7-pentamethoxyflavone (FLV5, 7.1 mg), 4’, (St. Paul, MN, USA). Hesperidin, neohesperidin, 5-dihydroxy-3, 3’, 6, 7, 8-pentamethoxyflavone and naringin were purchased from Nacalai Tesque Figure 1. Structures of isolated flavonoids from dried C. jabara fruit peels 6 Azuma S, et al. Table 1. Flavonoids isolated from dried C. jabara fruit peels (1 kg). Compound Amount (mg) Flavones FLV1 3, 3’, 4’, 5, 6, 7, 8-heptamethoxyflavone 265.8 FLV2 natsudaidain (3-hydroxy-3’, 4’, 5, 6, 7, 8-hexamethoxyflavone) 130.3 FLV3 5-hydroxy-3, 3’, 4’, 6, 7, 8-hexamethoxyflavone 29.3 FLV4 3, 3’, 4’, 5, 6, 7-hexamethoxyflavone 14.6 FLV5 8-hydroxy-3, 4’, 5, 6, 7-pentamethoxyflavone 7.1 FLV6 4’,5-dihydroxy-3, 3’, 6, 7, 8-pentamethoxyflavone 2.9 FLV7 retusin (5-hydroxy-3, 3’, 4’, 7-tetramethoxyflavone) 1.9 FLV8 nobiletin (3’, 4’, 5, 6, 7, 8-hexamethoxyflavone) 1.9 Flavanones FNN1 narirutin 17,700.0 FNN2 3’, 4’, 5, 6, 7, 8-hexamethoxyflavanone 32.1 FNN3 3’, 4’, 5, 6, 7-pentamethoxyflavanone 6.7 FNN4 4’, 5, 6, 7-tetramethoxyflavanone 1.4 Chalcones CHL1 2’-hydroxy-3, 3’, 4, 4’, 5’, 6’-hexamethoxychalcone 31.7 CHL2 2’-hydroxy-3, 4, 4’, 5’, 6’-pentamethoxychalcone 8.2 CHL3 2’-hydroxy-4, 4’, 5’, 6’-tetramethoxychalcone 7.8 (Kyoto, Japan). Dulbecco’s modified Eagle’s medium (TNF-α) ware obtained from BioLegend (San Diego, (DMEM) and penicillin-streptomycin mixed solution CA, USA). Human recombinant soluble epoxide (stabilized) were from Nacalai Tesque. Fetal bovine hydrolase (sEH) was purchased from Cayman serum was obtained from Biowest (Nuaillé, France). Chemical Company (Ann Arbor, MI, USA), and its Lipopolysaccharide (LPS) from Escherichia coli O55 substrate, (2S,3S)-trans-3-phenyl-2-oxiranylmethyl- was obtained from Wako Pure Chemical Industries 4-nitrophenyl carbonate (S-NEPC), was from Sigma- (Osaka, Japan). Griess reagent system was obtained Aldrich. Human recombinant chymase was obtained from Promega (Fitchburg, WI, USA). Cell Counting from Sigma-Aldrich, and its substrate, N-Succinyl- Kit-8 was from Dojindo Laboratories (Kumamoto, Ala-His-Pro-Phe-p-nitroanilide, was from Peptide Japan). RIPA buffer and protease inhibitor cocktail Institute (Osaka, Japan). Hyaluronidase from were purchased from Wako Pure Chemical. BCA bovine testes and Compound 48/80 were obtained Protein Assay Kit was obtained from Thermo Fisher from Sigma-Aldrich. Hyaluronic acid sodium salt Scientific (Waltham, MA, USA). Polyvinyliden from Rooster Comb was obtained from Wako Pure fluoride (PVDF) membrane was obtained from Bio- Chemical Industries. Rad (Hercules, CA, USA). Blocking one, a blocking solution for blot membrane, was obtained from HPLC analysis for quantification of Nacalai Tesque. Rabbit antibody to inducible nitric hesperidin, neohesperidin, naringin, and oxide synthase (iNOS) was obtained from Sigma- naringenin Aldrich (St. Louis, MO, USA), and anti-rabbit IgG HRP-linked whole antibody was from GE Healthcare Prior to the sample preparation, dried C. jabara (Buckinghamshire, UK). Monoclonal antibody to fruit peels were powdered. Amounts of hesperidin, neohesperidin, naringin, and naringenin were β-actin HRP conjugate was obtained from Wako Pure [15] Chemical Industries.
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